Recent New Developments on the Michael Addition of Sulfur and Selenium Nucleophiles

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  • Kamimura Akio
    Department of Applied Chemistry, Faculty of Engineering, Yamaguchi University

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  • 硫黄およびセレン求核剤を用いるマイケル付加反応の新展開
  • イオウ オヨビ セレンキュウカクザイ オ モチイル マイケル フカ ハンノウ ノ シン テンカイ

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Description

Recent development of synthetic reactions using the Michael addition of thiols or analogues is described. Nucloephilic attack of thiolate anions to α, β-unsaturated ketones or esters generates enolate anions which are active to perform aldol reaction when the reaction condition is kept away from protic media. High stereoselectivity as well as enantioselectivity is achieved for the Michael/aldol tandem reaction when appropriate reaction conditions are employed. High regioselective Michael addition of thiols to unsymmetric fumaric derivatives is also accomplished and the either of regioisomers is prepared in a highly selective manner. The thio-groups introduced by these reactions serve as a useful precursor of carbon radicals that efficiently undergo cyclization reaction to provide heterocyclic compounds diastereoselectively.

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